Natural Product: NPC187159

Natural Product ID:  NPC187159
Common Name:   Diosgenone
IUPAC Name:  
Synonyms:   Diosgenone
Molecular Formula:   C27H40O3
Standard InCHIKey:  AZXZUBZBLNFUPF-CLGLNXEMSA-N
Standard InCHI:  InChI=1S/C27H40O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h13,16-17,20-24H,5-12,14-15H2,1-4H3/t16-,17+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
Canonical SMILES:  C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CCC3=CC(=O)CC[C@@]3([C@H]1CC2)C)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32523 solanum violaceum Species Solanaceae Eukaryota PMID[23511021]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20 ug/ml 25798528
NPT2 Others Unspecified IC50 > 20 ug/ml 26090896
NPT81 Cell Line A549 Homo sapiens IC50 > 20 ug/ml 25614114
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 20 ug/ml 24957203
NPT65 Cell Line HepG2 Homo sapiens IC50 = 13.44 ug/ml 20696876

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC187159 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8725 High Similarity NPC163314
0.87 High Similarity NPC470309
0.8654 High Similarity NPC178981
0.8571 High Similarity NPC471398
0.8529 High Similarity NPC61411
0.8495 Intermediate Similarity NPC28227
0.8478 Intermediate Similarity NPC195640
0.8476 Intermediate Similarity NPC477944
0.8454 Intermediate Similarity NPC111684
0.8454 Intermediate Similarity NPC58052
0.837 Intermediate Similarity NPC323765
0.8333 Intermediate Similarity NPC242419
0.8333 Intermediate Similarity NPC235126
0.8302 Intermediate Similarity NPC260665
0.8283 Intermediate Similarity NPC271387
0.8283 Intermediate Similarity NPC153792
0.8269 Intermediate Similarity NPC246205
0.8247 Intermediate Similarity NPC304968
0.8247 Intermediate Similarity NPC472224
0.8247 Intermediate Similarity NPC128488
0.8247 Intermediate Similarity NPC472223
0.8242 Intermediate Similarity NPC24556
0.8235 Intermediate Similarity NPC121566
0.8235 Intermediate Similarity NPC228669
0.8235 Intermediate Similarity NPC100955
0.8235 Intermediate Similarity NPC164835
0.8229 Intermediate Similarity NPC218301
0.8224 Intermediate Similarity NPC477580
0.8218 Intermediate Similarity NPC22388
0.8172 Intermediate Similarity NPC470223
0.8155 Intermediate Similarity NPC95243
0.8155 Intermediate Similarity NPC63023
0.8137 Intermediate Similarity NPC140723
0.8085 Intermediate Similarity NPC470051
0.8085 Intermediate Similarity NPC470050
0.8061 Intermediate Similarity NPC111015
0.8 Intermediate Similarity NPC177818
0.7979 Intermediate Similarity NPC300985
0.7959 Intermediate Similarity NPC472225
0.7959 Intermediate Similarity NPC470923
0.7959 Intermediate Similarity NPC472226
0.7938 Intermediate Similarity NPC219495
0.7928 Intermediate Similarity NPC161738
0.79 Intermediate Similarity NPC322063
0.7895 Intermediate Similarity NPC473505
0.789 Intermediate Similarity NPC74727
0.7885 Intermediate Similarity NPC472227
0.7885 Intermediate Similarity NPC472228
0.7872 Intermediate Similarity NPC161423
0.7872 Intermediate Similarity NPC82902
0.7872 Intermediate Similarity NPC58841
0.7872 Intermediate Similarity NPC100391
0.7872 Intermediate Similarity NPC329043
0.7872 Intermediate Similarity NPC214043
0.7872 Intermediate Similarity NPC321187
0.7872 Intermediate Similarity NPC227064
0.7872 Intermediate Similarity NPC85774
0.7857 Intermediate Similarity NPC190442
0.7857 Intermediate Similarity NPC154101
0.785 Intermediate Similarity NPC475317
0.785 Intermediate Similarity NPC197428
0.785 Intermediate Similarity NPC52241
0.785 Intermediate Similarity NPC154856
0.785 Intermediate Similarity NPC27551
0.785 Intermediate Similarity NPC114961
0.7843 Intermediate Similarity NPC218383
0.7843 Intermediate Similarity NPC83709
0.7835 Intermediate Similarity NPC186688
0.7835 Intermediate Similarity NPC477943
0.7835 Intermediate Similarity NPC305039
0.783 Intermediate Similarity NPC295389
0.783 Intermediate Similarity NPC470269
0.783 Intermediate Similarity NPC258323
0.7826 Intermediate Similarity NPC47113
0.7826 Intermediate Similarity NPC174367
0.7822 Intermediate Similarity NPC475894
0.781 Intermediate Similarity NPC231530
0.781 Intermediate Similarity NPC475571
0.781 Intermediate Similarity NPC96377
0.781 Intermediate Similarity NPC278628
0.781 Intermediate Similarity NPC127790
0.781 Intermediate Similarity NPC162033
0.7798 Intermediate Similarity NPC52634
0.7798 Intermediate Similarity NPC73455
0.7798 Intermediate Similarity NPC200944
0.7789 Intermediate Similarity NPC474218
0.7788 Intermediate Similarity NPC182900
0.7788 Intermediate Similarity NPC476545
0.7788 Intermediate Similarity NPC476543
0.7788 Intermediate Similarity NPC36321
0.7788 Intermediate Similarity NPC476544
0.7788 Intermediate Similarity NPC249553
0.7778 Intermediate Similarity NPC229976
0.7768 Intermediate Similarity NPC319570
0.7767 Intermediate Similarity NPC176406
0.7767 Intermediate Similarity NPC474022
0.7767 Intermediate Similarity NPC474327
0.7766 Intermediate Similarity NPC470046
0.7766 Intermediate Similarity NPC470047
0.7755 Intermediate Similarity NPC171441
0.7745 Intermediate Similarity NPC176845
0.7739 Intermediate Similarity NPC190846
0.7739 Intermediate Similarity NPC277191
0.7732 Intermediate Similarity NPC470612
0.7732 Intermediate Similarity NPC470613
0.7727 Intermediate Similarity NPC165439
0.7723 Intermediate Similarity NPC73858
0.7723 Intermediate Similarity NPC42042
0.7719 Intermediate Similarity NPC305771
0.7719 Intermediate Similarity NPC28532
0.7719 Intermediate Similarity NPC15918
0.7719 Intermediate Similarity NPC169816
0.7719 Intermediate Similarity NPC94072
0.7719 Intermediate Similarity NPC475431
0.7714 Intermediate Similarity NPC255309
0.7714 Intermediate Similarity NPC223741
0.7708 Intermediate Similarity NPC264127
0.7708 Intermediate Similarity NPC31564
0.7708 Intermediate Similarity NPC474778
0.7708 Intermediate Similarity NPC474733
0.7708 Intermediate Similarity NPC474732
0.7708 Intermediate Similarity NPC469994
0.7708 Intermediate Similarity NPC145879
0.7706 Intermediate Similarity NPC210420
0.7706 Intermediate Similarity NPC474265
0.7706 Intermediate Similarity NPC130427
0.77 Intermediate Similarity NPC41649
0.77 Intermediate Similarity NPC56525
0.77 Intermediate Similarity NPC294266
0.7692 Intermediate Similarity NPC473888
0.7692 Intermediate Similarity NPC308351
0.7692 Intermediate Similarity NPC271266
0.7685 Intermediate Similarity NPC101450
0.7684 Intermediate Similarity NPC109512
0.7684 Intermediate Similarity NPC473246
0.7679 Intermediate Similarity NPC475632
0.7679 Intermediate Similarity NPC86020
0.7677 Intermediate Similarity NPC150383
0.767 Intermediate Similarity NPC167974
0.767 Intermediate Similarity NPC154072
0.7664 Intermediate Similarity NPC94529
0.7664 Intermediate Similarity NPC473288
0.766 Intermediate Similarity NPC100297
0.766 Intermediate Similarity NPC193347
0.7658 Intermediate Similarity NPC49492
0.7658 Intermediate Similarity NPC266728
0.7647 Intermediate Similarity NPC190554
0.7647 Intermediate Similarity NPC151488
0.7642 Intermediate Similarity NPC210178
0.7642 Intermediate Similarity NPC469874
0.7636 Intermediate Similarity NPC471173
0.7636 Intermediate Similarity NPC471627
0.7632 Intermediate Similarity NPC42675
0.7629 Intermediate Similarity NPC93778
0.7629 Intermediate Similarity NPC317590
0.7629 Intermediate Similarity NPC475740
0.7629 Intermediate Similarity NPC167877
0.7629 Intermediate Similarity NPC58063
0.7624 Intermediate Similarity NPC108141
0.7624 Intermediate Similarity NPC469599
0.7624 Intermediate Similarity NPC281134
0.7619 Intermediate Similarity NPC475701
0.7619 Intermediate Similarity NPC221421
0.7615 Intermediate Similarity NPC214797
0.7615 Intermediate Similarity NPC263827
0.7615 Intermediate Similarity NPC231589
0.7615 Intermediate Similarity NPC118860
0.7615 Intermediate Similarity NPC250481
0.7615 Intermediate Similarity NPC285410
0.7615 Intermediate Similarity NPC269466
0.7611 Intermediate Similarity NPC474179
0.7611 Intermediate Similarity NPC475834
0.7609 Intermediate Similarity NPC469996
0.7604 Intermediate Similarity NPC469948
0.76 Intermediate Similarity NPC475700
0.76 Intermediate Similarity NPC473678
0.76 Intermediate Similarity NPC470224
0.7593 Intermediate Similarity NPC258543
0.7593 Intermediate Similarity NPC112457
0.7593 Intermediate Similarity NPC241927
0.7586 Intermediate Similarity NPC475194
0.7573 Intermediate Similarity NPC70733
0.7573 Intermediate Similarity NPC56071
0.757 Intermediate Similarity NPC220974
0.757 Intermediate Similarity NPC471601
0.7568 Intermediate Similarity NPC326542
0.7568 Intermediate Similarity NPC474557
0.7568 Intermediate Similarity NPC473882
0.7565 Intermediate Similarity NPC313528
0.7565 Intermediate Similarity NPC216866
0.7551 Intermediate Similarity NPC97884
0.7551 Intermediate Similarity NPC472220
0.7551 Intermediate Similarity NPC328313
0.7551 Intermediate Similarity NPC474845
0.7547 Intermediate Similarity NPC474464
0.7547 Intermediate Similarity NPC235889
0.7547 Intermediate Similarity NPC222161
0.7545 Intermediate Similarity NPC207251
0.7545 Intermediate Similarity NPC170487
0.7544 Intermediate Similarity NPC475187

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC187159 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8614 High Similarity NPD6412 Phase 2
0.8495 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8495 Intermediate Similarity NPD6903 Approved
0.8478 Intermediate Similarity NPD5330 Approved
0.8478 Intermediate Similarity NPD7521 Approved
0.8478 Intermediate Similarity NPD6409 Approved
0.8478 Intermediate Similarity NPD6684 Approved
0.8478 Intermediate Similarity NPD7334 Approved
0.8478 Intermediate Similarity NPD7146 Approved
0.8155 Intermediate Similarity NPD6008 Approved
0.798 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD6672 Approved
0.7917 Intermediate Similarity NPD5737 Approved
0.7872 Intermediate Similarity NPD3666 Approved
0.7872 Intermediate Similarity NPD3133 Approved
0.7872 Intermediate Similarity NPD3665 Phase 1
0.7857 Intermediate Similarity NPD6059 Approved
0.7857 Intermediate Similarity NPD6054 Approved
0.7835 Intermediate Similarity NPD6673 Approved
0.7835 Intermediate Similarity NPD6080 Approved
0.7835 Intermediate Similarity NPD6904 Approved
0.7755 Intermediate Similarity NPD5207 Approved
0.7732 Intermediate Similarity NPD5208 Approved
0.7719 Intermediate Similarity NPD6370 Approved
0.7708 Intermediate Similarity NPD6098 Approved
0.77 Intermediate Similarity NPD6001 Approved
0.766 Intermediate Similarity NPD4223 Phase 3
0.766 Intermediate Similarity NPD4221 Approved
0.7647 Intermediate Similarity NPD6083 Phase 2
0.7647 Intermediate Similarity NPD6084 Phase 2
0.7632 Intermediate Similarity NPD6015 Approved
0.7632 Intermediate Similarity NPD6016 Approved
0.7604 Intermediate Similarity NPD5329 Approved
0.76 Intermediate Similarity NPD4202 Approved
0.76 Intermediate Similarity NPD6399 Phase 3
0.7586 Intermediate Similarity NPD7492 Approved
0.7565 Intermediate Similarity NPD5988 Approved
0.7545 Intermediate Similarity NPD6882 Approved
0.7542 Intermediate Similarity NPD7736 Approved
0.7521 Intermediate Similarity NPD6616 Approved
0.75 Intermediate Similarity NPD4197 Approved
0.75 Intermediate Similarity NPD6050 Approved
0.75 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6067 Discontinued
0.75 Intermediate Similarity NPD5693 Phase 1
0.75 Intermediate Similarity NPD4786 Approved
0.7477 Intermediate Similarity NPD5739 Approved
0.7477 Intermediate Similarity NPD6675 Approved
0.7477 Intermediate Similarity NPD7128 Approved
0.7477 Intermediate Similarity NPD6402 Approved
0.7475 Intermediate Similarity NPD4753 Phase 2
0.7475 Intermediate Similarity NPD5328 Approved
0.7458 Intermediate Similarity NPD7078 Approved
0.7458 Intermediate Similarity NPD8293 Discontinued
0.7451 Intermediate Similarity NPD5695 Phase 3
0.7434 Intermediate Similarity NPD6009 Approved
0.7404 Intermediate Similarity NPD5696 Approved
0.74 Intermediate Similarity NPD5692 Phase 3
0.7395 Intermediate Similarity NPD6033 Approved
0.7373 Intermediate Similarity NPD7507 Approved
0.7353 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7900 Approved
0.7347 Intermediate Similarity NPD5205 Approved
0.7347 Intermediate Similarity NPD4693 Phase 3
0.7347 Intermediate Similarity NPD4138 Approved
0.7347 Intermediate Similarity NPD4689 Approved
0.7347 Intermediate Similarity NPD4688 Approved
0.7347 Intermediate Similarity NPD4690 Approved
0.7347 Intermediate Similarity NPD3618 Phase 1
0.7339 Intermediate Similarity NPD6881 Approved
0.7339 Intermediate Similarity NPD6899 Approved
0.7327 Intermediate Similarity NPD5694 Approved
0.7327 Intermediate Similarity NPD6079 Approved
0.7308 Intermediate Similarity NPD4755 Approved
0.7292 Intermediate Similarity NPD3667 Approved
0.729 Intermediate Similarity NPD6052 Approved
0.7273 Intermediate Similarity NPD6373 Approved
0.7273 Intermediate Similarity NPD6372 Approved
0.7248 Intermediate Similarity NPD5701 Approved
0.7248 Intermediate Similarity NPD5697 Approved
0.7238 Intermediate Similarity NPD7638 Approved
0.7222 Intermediate Similarity NPD4747 Approved
0.7207 Intermediate Similarity NPD7290 Approved
0.7207 Intermediate Similarity NPD6883 Approved
0.7207 Intermediate Similarity NPD7102 Approved
0.719 Intermediate Similarity NPD7319 Approved
0.7184 Intermediate Similarity NPD7748 Approved
0.7182 Intermediate Similarity NPD6686 Approved
0.7182 Intermediate Similarity NPD6011 Approved
0.7172 Intermediate Similarity NPD5690 Phase 2
0.7172 Intermediate Similarity NPD5279 Phase 3
0.7172 Intermediate Similarity NPD4694 Approved
0.7172 Intermediate Similarity NPD5280 Approved
0.717 Intermediate Similarity NPD4700 Approved
0.717 Intermediate Similarity NPD5286 Approved
0.717 Intermediate Similarity NPD7640 Approved
0.717 Intermediate Similarity NPD4696 Approved
0.717 Intermediate Similarity NPD7639 Approved
0.717 Intermediate Similarity NPD5285 Approved
0.7168 Intermediate Similarity NPD4632 Approved
0.7157 Intermediate Similarity NPD5281 Approved
0.7157 Intermediate Similarity NPD5284 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7143 Intermediate Similarity NPD8130 Phase 1
0.7143 Intermediate Similarity NPD6869 Approved
0.7143 Intermediate Similarity NPD6617 Approved
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD3668 Phase 3
0.7143 Intermediate Similarity NPD6650 Approved
0.7131 Intermediate Similarity NPD5956 Approved
0.7117 Intermediate Similarity NPD6013 Approved
0.7117 Intermediate Similarity NPD6014 Approved
0.7117 Intermediate Similarity NPD6012 Approved
0.7115 Intermediate Similarity NPD5210 Approved
0.7115 Intermediate Similarity NPD4629 Approved
0.7111 Intermediate Similarity NPD4137 Phase 3
0.7103 Intermediate Similarity NPD5223 Approved
0.71 Intermediate Similarity NPD3573 Approved
0.708 Intermediate Similarity NPD8297 Approved
0.7069 Intermediate Similarity NPD7328 Approved
0.7069 Intermediate Similarity NPD7327 Approved
0.7041 Intermediate Similarity NPD4788 Approved
0.7037 Intermediate Similarity NPD5224 Approved
0.7037 Intermediate Similarity NPD5211 Phase 2
0.7037 Intermediate Similarity NPD4633 Approved
0.7037 Intermediate Similarity NPD5225 Approved
0.7037 Intermediate Similarity NPD5226 Approved
0.7033 Intermediate Similarity NPD4691 Approved
0.7009 Intermediate Similarity NPD7516 Approved
0.699 Remote Similarity NPD7515 Phase 2
0.6989 Remote Similarity NPD5733 Approved
0.6979 Remote Similarity NPD4195 Approved
0.6972 Remote Similarity NPD4754 Approved
0.6972 Remote Similarity NPD5174 Approved
0.6972 Remote Similarity NPD5175 Approved
0.6961 Remote Similarity NPD6051 Approved
0.6952 Remote Similarity NPD5654 Approved
0.6949 Remote Similarity NPD6319 Approved
0.6949 Remote Similarity NPD8294 Approved
0.6949 Remote Similarity NPD8377 Approved
0.693 Remote Similarity NPD6053 Discontinued
0.6917 Remote Similarity NPD7604 Phase 2
0.6909 Remote Similarity NPD5141 Approved
0.6907 Remote Similarity NPD6928 Phase 2
0.6903 Remote Similarity NPD4634 Approved
0.6891 Remote Similarity NPD8379 Approved
0.6891 Remote Similarity NPD5983 Phase 2
0.6891 Remote Similarity NPD8033 Approved
0.6891 Remote Similarity NPD8335 Approved
0.6891 Remote Similarity NPD7503 Approved
0.6891 Remote Similarity NPD8296 Approved
0.6891 Remote Similarity NPD8380 Approved
0.6891 Remote Similarity NPD8378 Approved
0.6887 Remote Similarity NPD5222 Approved
0.6887 Remote Similarity NPD4697 Phase 3
0.6887 Remote Similarity NPD5221 Approved
0.6887 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3617 Approved
0.687 Remote Similarity NPD6858 Approved
0.687 Remote Similarity NPD7094 Approved
0.6847 Remote Similarity NPD4768 Approved
0.6847 Remote Similarity NPD4767 Approved
0.6832 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6827 Remote Similarity NPD8034 Phase 2
0.6827 Remote Similarity NPD8035 Phase 2
0.6822 Remote Similarity NPD5959 Approved
0.6822 Remote Similarity NPD5173 Approved
0.6814 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4687 Approved
0.6809 Remote Similarity NPD4058 Approved
0.6803 Remote Similarity NPD6336 Discontinued
0.6786 Remote Similarity NPD6614 Approved
0.678 Remote Similarity NPD6335 Approved
0.6777 Remote Similarity NPD8328 Phase 3
0.6774 Remote Similarity NPD5777 Approved
0.6774 Remote Similarity NPD5276 Approved
0.6768 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6274 Approved
0.675 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6733 Remote Similarity NPD1694 Approved
0.6733 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4096 Approved
0.6726 Remote Similarity NPD4730 Approved
0.6726 Remote Similarity NPD4729 Approved
0.6726 Remote Similarity NPD5128 Approved
0.6724 Remote Similarity NPD8133 Approved
0.6723 Remote Similarity NPD7100 Approved
0.6723 Remote Similarity NPD7101 Approved
0.6698 Remote Similarity NPD5282 Discontinued
0.6695 Remote Similarity NPD6317 Approved
0.6694 Remote Similarity NPD8337 Approved
0.6694 Remote Similarity NPD8336 Approved
0.6667 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4139 Approved
0.6667 Remote Similarity NPD4692 Approved
0.6639 Remote Similarity NPD6314 Approved
0.6639 Remote Similarity NPD6313 Approved

Structure

External Identifiers

PubChem CID   10251134
ChEMBL   CHEMBL1915879
ZINC  

Physicochemical Properties

Molecular Weight:  412.30
ALogP:  0.9333
MLogP:  4.1
XLogP:  6.034
# Rotatable Bonds:  4
Polar Surface Area:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  30

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